This invention relates to certain heterotricyclic compounds, their N-oxides, agriculturally suitable salts and compositions, and methods of their use for controlling undesirable vegetation.
The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
WO 94/04524 discloses herbicidal cyclohexanedione derivatives of Formula i as herbicides: ##STR2##
wherein, inter alia,
R.sub.1 is C.sub.1 -C.sub.6 alkyl; PA1 R.sub.2 is C.sub.1 -C.sub.4 alkyl; PA1 R.sub.3 -R.sub.5 are H or C.sub.1 -C.sub.4 alkyl; and PA1 n is 0, 1 or 2. PA1 X is O, S(O).sub.n, N(C.sub.1 -C.sub.2 alkyl), N, CH or CH.sub.2 optionally substituted with 1-2 C.sub.1 -C.sub.2 alkyl; PA1 A is O or S(O).sub.n ; PA1 B is S(O).sub.n ; PA1 each R.sup.1 is independently C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, S(O).sub.n R.sup.17, SO.sub.2 N(R.sup.13).sub.2, halogen, cyano or nitro; PA1 each R.sup.2 is independently C.sub.1 -C.sub.3 alkyl; PA1 each R.sup.3 is independently C.sub.1 -C.sub.2 alkyl; PA1 R.sup.4 is OR.sup.14, SH, S(O).sub.n R.sup.17, halogen or NR.sup.15 R.sup.16 ; or R.sup.4 is phenylthio or phenylsulfonyl, each optionally substituted with C.sub.1 -C.sub.3 alkyl, halogen, cyano or nitro; PA1 each R.sup.5 is independently H, C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.1 -C.sub.3 alkoxy, formyl, C.sub.2 -C.sub.6 alkoxycarbonyl, --CH.sub.2 (C.sub.1 -C.sub.3 alkoxy), --CH(C.sub.1 -C.sub.3 alkoxy).sub.2, C.sub.1 -C.sub.3 alkylthio, cyano or halogen; or when two R.sup.5 are attached to the same carbon atom, then said R.sup.5 pair can be taken together to form --OCH.sub.2 CH.sub.2 O--, --OCH.sub.2 CH.sub.2 CH.sub.2 O--, --SCH.sub.2 CH.sub.2 S--or --SCH.sub.2 CH.sub.2 CH.sub.2 S--, each group optionally substituted with 1-4 CH.sub.3 ; PA1 R.sup.6 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, formyl, C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.2 -C.sub.6 alkylaminocarbonyl, C.sub.3 -C.sub.7 dialkylaminocarbonyl or SO.sub.2 R.sup.17 ; or R.sup.6 is phenyl, benzyl, benzoyl, --CH.sub.2 C(O)phenyl or phenylsulfonyl, each optionally substituted on the phenyl ring with C.sub.1 -C.sub.3 alkyl, halogen, cyano, or nitro; PA1 R.sup.7 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl or --CH.sub.2 CH.sub.2 OR.sup.13 ; or R.sup.7 is phenyl or benzyl, each optionally substituted on the phenyl ring with C.sub.1 -C.sub.3 alkyl, halogen, cyano or nitro; PA1 R.sup.8 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, halogen, cyano or nitro; PA1 R.sup.9 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl or C.sub.3 -C.sub.6 halocycloalkyl; PA1 R.sup.10 is H, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.2 -C.sub.6 haloalkoxycarbonyl, CO.sub.2 H or cyano; PA1 R.sup.11 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 halocycloalkyl or C.sub.3 -C.sub.6 cycloalkyl optionally substituted with 1-4 C.sub.1 -C.sub.3 alkyl; PA1 R.sup.12 is cyano, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.2 -C.sub.6 alkylcarbonyl, S(O).sub.n R.sup.16 or C(O)NR.sup.15 R.sup.16 ; each R.sup.13 is independently H or C.sub.1 -C.sub.6 alkyl; PA1 R.sup.14 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, formyl, C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C(O)NR.sup.15 R.sup.16 or SO.sub.2 R.sup.17 ; or R.sup.14 is phenyl, benzyl, benzoyl, --CH.sub.2 C(O)phenyl or phenylsulfonyl, each optionally substituted on the phenyl ring with C.sub.1 -C.sub.3 alkyl, halogen, cyano or nitro; PA1 R.sup.15 is H or C.sub.1 -C.sub.6 alkyl; PA1 R.sup.16 is C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy; or PA1 R.sup.15 and R.sup.16 can be taken together as --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA1 R.sup.17 is C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 haloalkyl; PA1 m is 0, 1 or 2; PA1 each n is independently 0, 1 or 2; PA1 p is 0, 1 or 2; PA1 q is 1 or 2; PA1 r is 0, 1,2or 3; and PA1 s is 0, 1,2,3or 4; PA1 provided that when m is 0 then X is other than N or CH; and PA1 wherein the dashed line in Formula I signifies either a single or double bond. PA1 Preferred 1. Compounds of Formula I above, and N-oxides and agriculturally suitable salts thereof, wherein: PA1 Preferred 2. Compounds of Preferred 1 wherein: PA1 Preferred 3. Compounds of Preferred 2 wherein: PA1 Preferred 4. Compounds of Preferred 2 wherein: PA1 L is a leaving group such as C.sub.1 -C.sub.4 alkoxy (e.g., OC.sub.2 H.sub.5) or N,N-dialkylamino (e.g., dimethyl amino) R.sup.10a is H, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.2 -C.sub.6 haloalkoxycarbonyl or CONH.sub.2
The heterotricyclic compounds of the present invention are not disclosed in this publication.